SU368254A1 - Способ получения соединений тиофосфамида с алкалоидами чистотела большого - Google Patents
Способ получения соединений тиофосфамида с алкалоидами чистотела большогоInfo
- Publication number
- SU368254A1 SU368254A1 SU1330542A SU1330542A SU368254A1 SU 368254 A1 SU368254 A1 SU 368254A1 SU 1330542 A SU1330542 A SU 1330542A SU 1330542 A SU1330542 A SU 1330542A SU 368254 A1 SU368254 A1 SU 368254A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- thiophosphamide
- alkaloids
- celandine
- soluble
- chloroform
- Prior art date
Links
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 title claims 20
- 229930013930 alkaloid Natural products 0.000 title claims 17
- 229960001196 thiotepa Drugs 0.000 title claims 17
- 238000000034 method Methods 0.000 title claims 8
- 150000001875 compounds Chemical class 0.000 title claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 241001233914 Chelidonium majus Species 0.000 claims 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 10
- INVGWHRKADIJHF-UHFFFAOYSA-N Sanguinarin Chemical compound C1=C2OCOC2=CC2=C3[N+](C)=CC4=C(OCO5)C5=CC=C4C3=CC=C21 INVGWHRKADIJHF-UHFFFAOYSA-N 0.000 claims 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- FCEXWTOTHXCQCQ-UHFFFAOYSA-N Ethoxydihydrosanguinarine Natural products C12=CC=C3OCOC3=C2C(OCC)N(C)C(C2=C3)=C1C=CC2=CC1=C3OCO1 FCEXWTOTHXCQCQ-UHFFFAOYSA-N 0.000 claims 5
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 claims 5
- 229940093265 berberine Drugs 0.000 claims 5
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 claims 5
- 229940068560 greater celandine Drugs 0.000 claims 5
- 230000003993 interaction Effects 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- 229940084560 sanguinarine Drugs 0.000 claims 5
- YZRQUTZNTDAYPJ-UHFFFAOYSA-N sanguinarine pseudobase Natural products C1=C2OCOC2=CC2=C3N(C)C(O)C4=C(OCO5)C5=CC=C4C3=CC=C21 YZRQUTZNTDAYPJ-UHFFFAOYSA-N 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 238000010992 reflux Methods 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 238000007098 aminolysis reaction Methods 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- -1 nitrogen amine Chemical class 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229910004814 HzPO4 Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000003797 alkaloid derivatives Chemical class 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 238000005452 bending Methods 0.000 claims 1
- AQHMSOCWYFWQRO-UHFFFAOYSA-N benzene;methylsulfinylmethane Chemical compound CS(C)=O.C1=CC=CC=C1 AQHMSOCWYFWQRO-UHFFFAOYSA-N 0.000 claims 1
- 150000003836 berberines Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 230000001766 physiological effect Effects 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/564—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/62—Isoquinoline or hydrogenated isoquinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G5/00—Alkaloids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1330542A SU368254A1 (ru) | 1969-06-16 | 1969-06-16 | Способ получения соединений тиофосфамида с алкалоидами чистотела большого |
| DE19702028330 DE2028330C3 (de) | 1969-06-16 | 1970-06-09 | Thiophosphorsäureimid-Isochinolin-Addukte und diese enthaltende Mittel |
| CH883470A CH553225A (de) | 1969-06-16 | 1970-06-11 | Verfahren zur herstellung von additionsverbindungen von thiophosphorsaeure-tris-aethylenamid und alkaloiden. |
| PL14127270A PL81014B1 (enrdf_load_stackoverflow) | 1969-06-16 | 1970-06-12 | |
| GB2882870A GB1304064A (enrdf_load_stackoverflow) | 1969-06-16 | 1970-06-15 | |
| SE828570A SE367637B (enrdf_load_stackoverflow) | 1969-06-16 | 1970-06-15 | |
| FR7022029A FR2052972B1 (enrdf_load_stackoverflow) | 1969-06-16 | 1970-06-16 | |
| CS420870A CS155618B1 (enrdf_load_stackoverflow) | 1969-06-16 | 1970-06-16 | |
| BE752064D BE752064A (fr) | 1969-06-16 | 1970-06-16 | Derives thiophosphamides des alcaloides de la serie de l'isoquinoleine,leur preparation et leurs applications |
| RO6364670A RO57382A (enrdf_load_stackoverflow) | 1969-06-16 | 1970-06-16 | |
| US264482A US3865830A (en) | 1969-06-16 | 1972-06-20 | Thiophosphamide derivatives of isoquinoline alkaloids, method of producing and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1330542A SU368254A1 (ru) | 1969-06-16 | 1969-06-16 | Способ получения соединений тиофосфамида с алкалоидами чистотела большого |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU368254A1 true SU368254A1 (ru) | 1973-01-26 |
Family
ID=20445753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1330542A SU368254A1 (ru) | 1969-06-16 | 1969-06-16 | Способ получения соединений тиофосфамида с алкалоидами чистотела большого |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE752064A (enrdf_load_stackoverflow) |
| CH (1) | CH553225A (enrdf_load_stackoverflow) |
| CS (1) | CS155618B1 (enrdf_load_stackoverflow) |
| FR (1) | FR2052972B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1304064A (enrdf_load_stackoverflow) |
| PL (1) | PL81014B1 (enrdf_load_stackoverflow) |
| RO (1) | RO57382A (enrdf_load_stackoverflow) |
| SE (1) | SE367637B (enrdf_load_stackoverflow) |
| SU (1) | SU368254A1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH695417A5 (de) * | 2001-11-15 | 2006-05-15 | Ddr Wassyl Nowicky Dipl Ing | Verfahren zur Umsetzung von Alkaloiden. |
| EP1459753A1 (en) | 2003-03-18 | 2004-09-22 | Nowicky, Wassyl, Dipl.-Ing. DDr. | Quaternary chelidonine and alkaloid derivatives, process for their preparation and their use in the manufacture of medicaments |
-
1969
- 1969-06-16 SU SU1330542A patent/SU368254A1/ru active
-
1970
- 1970-06-11 CH CH883470A patent/CH553225A/xx unknown
- 1970-06-12 PL PL14127270A patent/PL81014B1/pl unknown
- 1970-06-15 SE SE828570A patent/SE367637B/xx unknown
- 1970-06-15 GB GB2882870A patent/GB1304064A/en not_active Expired
- 1970-06-16 BE BE752064D patent/BE752064A/xx unknown
- 1970-06-16 FR FR7022029A patent/FR2052972B1/fr not_active Expired
- 1970-06-16 RO RO6364670A patent/RO57382A/ro unknown
- 1970-06-16 CS CS420870A patent/CS155618B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH553225A (de) | 1974-08-30 |
| SE367637B (enrdf_load_stackoverflow) | 1974-06-04 |
| DE2028330B2 (de) | 1977-02-03 |
| BE752064A (fr) | 1970-12-16 |
| FR2052972A1 (enrdf_load_stackoverflow) | 1971-04-16 |
| RO57382A (enrdf_load_stackoverflow) | 1975-01-15 |
| DE2028330A1 (de) | 1971-05-27 |
| GB1304064A (enrdf_load_stackoverflow) | 1973-01-24 |
| PL81014B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| FR2052972B1 (enrdf_load_stackoverflow) | 1973-08-10 |
| CS155618B1 (enrdf_load_stackoverflow) | 1974-05-30 |
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